4-Chloroaniline → HCID 178512018, compound

HRID 1062419Notes

Reaction equation

HRID 1062419 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.CC[Mg+].[Br-].[Cl:13][C:14]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:15]=1[C:16]#[N:17]>>[Cl:13][C:14]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:15]=1[C:16](=[NH:17])[NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 78124-ChloroanilineHCID 810502,4-DichlorobenzonitrileHCID 178461630HCID 178461630, compound

Product 1

HCID 178512018HCID 178512018, compoundYield 103.4%

Procedure

Under argon, 4-chloroaniline (6.67 g, 52.5 mmol) was slowly added to EtMgBr (52 mL, 1 M in THF, 52 mmol) portion wise. After the solution was stirred for 0.5 h, 2,4-dichlorobenzonitrile (9.03 g, 52.5 mmol) was added. The resulting solution was stirred at rt overnight. The reaction mixture was carefully quenched with water and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated. Crude product (16.26 g,) was obtained as a sticky brown foam which was used without purification for the next step. LC-MS m/z 299.3 (MH+), retention time 1.75 min (MDLC 1); 1H NMR (300 MHz, CDCl3) δ 4.92 (2H, br), 7.09-7.51 (7H, m).

Workup

  1. stirringThe resulting solution was stirred at rt overnight
  2. customThe reaction mixture was carefully quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-25709a2f90f44b57aee632be2bcded14
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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